4-amino-2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester | 886053-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-amino-2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester
• 英文别名: ethyl 4-amino-2-[6-(2-tert-butoxy-2-oxoethoxy)-3-oxo-3H-xanthen-9-yl]benzoate；Ethyl 4-amino-2-[3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-6-oxoxanthen-9-yl]benzoate
• CAS: 886053-23-2
• 化学式: C₂₈H₂₇NO₇
• 分子量: 489.525
• InChiKey: XRKWDYMZCQRQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(6-carboxymethoxy-3-oxo-3H-xanthen-9-yl)-4-(2-{[2-(9H-fluoren-9-ylmethoxycarbonyl-amino)-ethylcarbamoyl]-methoxy}-acetylamino)-benzoic acid ethyl ester
  参考文献：
  名称：

  Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates

  摘要：

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.037
• 作为产物：
  描述：

  6-aminofluorescein 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 4-amino-2-(6-tert-butoxycarbonylmethoxy-3-oxo-3H-xanthen-9-yl)-benzoic acid ethyl ester
  参考文献：
  名称：

  Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates

  摘要：

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.037

文献信息

• Fluorescein-Based Compounds And Their Use For Peptide Synthesis
  申请人：Balakirev Maxim

  公开号：US20080275215A1

  公开（公告）日：2008-11-06

  The present invention is related to new fluorescein derivatives, the method for producing such derivatives and their use for the synthesis of fluorogenic peptides and in particular protease substrates and peptide ligands.

  本发明涉及新的荧光素衍生物，以及制备这些衍生物的方法及其用于合成荧光基肽和特别是蛋白酶底物和肽配体的用途。
• Synthesis of SERS active nanoparticles for detection of biomolecules
  作者：Joanna Wrzesien、Duncan Graham

  DOI：10.1016/j.tet.2011.11.053

  日期：2012.1

  Surface Enhanced Raman Scattering (SERS) can be used to detect specific DNA sequences by methods based on hybridisation of oligonucleotide functionalized nanoparticles to complementary DNA sequences. The problem, which has to be overcome to use this technique is that DNA is not strongly SERS active. This is due to the lack of a visible chromophore and presence of the highly negatively charged phosphate backbone, which prevents the electrostatic interaction with the metal surface necessary for the enhancement. To obtain SERS active DNA a label containing a surface seeking group, to allow adsorption of DNA on a metal surface, and a chromophore has to be attached to the DNA strand. Here we report the synthesis of three linkers containing a Raman tag [the following fluorophores were used for this purpose due to the fluorescence quenching ability of metallic nanoparticles: fluorescein, 6-aminofluorescein and tetramethylrhodamine (TAMRA)], surface complexing group (cyclic disulphide thioctic acid) and a chemical functionality for attachment of DNA (carboxyl group). Each of the linkers also contain poly(ethylene glycol) (PEG) (3 mer), which reduces non-specific adsorption of molecules to the surface of the nanoparticles and provides colloidal stability. The synthesized linkers were used to functionalize gold citrate (18 and 50 nm), silver citrate (40 nm) and silver EDTA (35 nm) nanoparticles. All of the conjugates exhibit high stability, gave good SERS responses at laser excitation frequencies of 514 and 633 nm and could be conjugated to amino-modified oligonucleotides in the presence of the commonly used (N-(3-dimethylaminopropyl)-N'-ethyl carbodiimide hydrochloride-EDC center dot HCl with N-hydroxysulfosuccinimide or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-DMT MM, which has not been used for bioconjugate preparation previously. This approach is less time consuming and less expensive than previously used protocols and does not require the formation of a mixed layer of oligonucleotides and Raman reporter on the metal surface. Additionally the presence of a reactive functionality within the linker structure makes it possible to conjugate the linker to other biomolecules of interest such as proteins. (C) 2011 Elsevier Ltd. All rights reserved.
• Fluorescein-based compounds and their use for peptide synthesis
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE

  公开号：EP1749870B1

  公开（公告）日：2008-05-14
• Fluorescein-based amino acids for solid phase synthesis of fluorogenic protease substrates
  作者：Olga N. Burchak、Laurent Mugherli、François Chatelain、Maxim Y. Balakirev

  DOI：10.1016/j.bmc.2005.11.037

  日期：2006.4

  An efficient synthesis of new type fluorescent amino acids is described. The Fmoc-protected dyes can be prepared in a four-step procedure with similar to 30% overall yield from aminofluoresceins and other inexpensive commercially available precursors. The dyes are much more photostable compared to fluorescein and exhibit constant pH-independent fluorescence that is advantageous in biological applications. The Fmoc-protected fluorescent amino acids are ready for use in solid phase peptide synthesis. As a proof of concept, a fluorogenic papain Substrate was synthesized and employed for on-bead detection of the protease activity. By using a novel technique for quantitative analysis of bead fluorescence, a similar to 2.7-fold increase in mean bead brightness was measured and was attributed to Substrate cleavage by papain. The new type fluorescent amino acids seem to be a promising tool for the synthesis of fluorescent peptide ligands and fluorogenic protease substrates. (c) 2005 Elsevier Ltd. All rights reserved.